Monodictyochromes A and B, dimeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis.
Investigations of the marine-derived fungus Monodictys putredinis led to the isolation of two novel dimeric chromanones (1, 2) that consist of two uniquely modified xanthone-derived units. The structures were elucidated by extensive spectroscopic measurements including NOE experiments and CD analysis to deduce the configuration. The compounds (1, 2) were examined for their cancer chemopreventive potential and shown to inhibit cytochrome P450 1A activity with IC(50) values of 5.3 and 7.5 μM, respectively. In addition, both compounds displayed moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells, with CD values (concentration required to double the specific activity of QR) of 22.1 and 24.8 μM, respectively. Compound 1 was slightly less potent than compound 2 in inhibiting aromatase activity, with IC(50) values of 24.4 and 16.5 μM.
Pontius
Alexander
A
Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, Germany.
Krick
Anja
A
Mesry
Ronak
R
Kehraus
Stefan
S
Foegen
Silke E
SE
Müller
Michael
M
Klimo
Karin
K
Gerhäuser
Clarissa
C
König
Gabriele M
GM
D000818:Animals; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047072:Aromatase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D000460:Chlorophyta / Q000382:microbiology; D002867:Chromones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004790:Enzyme Induction / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis / Q000187:drug effects; D013030:Spain; D044004:Xanthones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D016588:Anticarcinogenic Agents; D047072:Aromatase Inhibitors; D002867:Chromones; D044004:Xanthones; C567990:monodictyochrome A; C567991:monodictyochrome B; D016660:NAD(P)H Dehydrogenase (Quinone)